Diethyl {(4-methoxy­phen­yl)[5-(4-nitro­phen­yl)-1,3,4-thia­diazol-2-ylamino]meth­yl}phospho­nate

Li-He Yin; Rong Wan; Feng Han; Bin Wang; Jin-Tang Wang

doi:10.1107/S1600536808017364

. 2008 Jul 5;64(Pt 8):o1376. doi: 10.1107/S1600536808017364

Diethyl {(4-methoxyphenyl)[5-(4-nitrophenyl)-1,3,4-thiadiazol-2-ylamino]methyl}phosphonate

Li-He Yin ^a, Rong Wan ^a,^*, Feng Han ^a, Bin Wang ^a, Jin-Tang Wang ^a

PMCID: PMC2962010 PMID: 21203097

Abstract

The title compound, C₂₀H₂₃N₄O₆PS, was synthesized by the reaction of N-(4-methoxybenzylidene)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine and diethyl phosphite. The thiadiazole and nitro-substituted phenyl rings in the molecule are approximately coplanar, the dihedral angle being 5.3 (2)°. The dihedral angle formed by the mean plane through all non-H atoms of both the thiadiazole and the nitro-substituted phenyl ring with the plane of the methoxy-substituted phenyl ring is 48.9 (2)°. In the crystal structure, molecules form centrosymmetric dimers as a result of N—H⋯O bonds involving amine H and phosphine oxide O atoms.

Related literature

For related literature, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶).

Experimental

Crystal data

C₂₀H₂₃N₄O₆PS
M _r = 478.45
Monoclinic,
a = 11.481 (2) Å
b = 19.426 (4) Å
c = 11.960 (2) Å
β = 117.08 (3)°
V = 2375.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.930, T _max = 0.976
4497 measured reflections
4276 independent reflections
2330 reflections with I > 2σ(I)
R _int = 0.064
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.146
S = 1.03
4276 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius,1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017364/ya2071sup1.cif

e-64-o1376-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017364/ya2071Isup2.hkl

e-64-o1376-Isup2.hkl^{(209.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.86	1.94	2.782 (6)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Professor Hua-Qin Wang of Nanjing University, for providing the Enraf–Nonius CAD-4 diffractometer for this research project.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives represent an interesting class of biologically important compounds, which often exhibit insecticidal, fungicidal and other biological activities (Nakagawa et al., 1996; Wang et al., 1999).

We report here the X-ray structure of the title compound,(I)(Fig. 1). The thiadiazole and nitro-substituted phenyl rings in the molecule of (I) are approximately coplanar: the dihedral angle between the C11—C16 and S/C10/N2/N3/C9 planes being 5.3 (2)°, the maximum deviation from the mean plane N1/C9/C10/N2/N3/S/C11/C12/C13/C14/C15/C16 does not exceed 0.11 Å. The dihedral angle formed by the latter plane with the plane of the methoxy- substituted phenyl ring C2—C7 is equal to 48.9 (2) °.

In the crystal structure, molecules of (I) form centrosymmetric dimers due to N—H···O bonds involving amine hydrogen and phosphineoxide oxygen [N1···O5ⁱ 2.782 (6) Å; symmetry code (i): -x, -y, -z].

Experimental

N-(4-methoxybenzylidene)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (2 mmol) and diethyl phosphite (5 mmol) were mixed in a 25 ml flask (without any solvent),and kept in the oil bath at 90°C for 6 h. After cooling, the crude product (I) precipitated and was filtered. Pure compound (I) was obtained by recrystallization from ethanol(20 ml). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.